Trifluoroacetic acid → HCID 9851229, compound

HRID 2227868Notes

Reaction equation

HRID 2227868 reaction equation
C(OC([NH:8][CH2:9][CH2:10][C:11]([N:13]([CH2:32][C:33]([NH:35][CH2:36][C:37]1[CH:48]=[CH:47][C:40]([C:41]([O:43][CH2:44][C:45]#[N:46])=[O:42])=[C:39]([OH:49])[CH:38]=1)=[O:34])[CH2:14][C:15](=[O:31])[NH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([O:26][CH2:27][C:28]#[N:29])=[O:25])=[C:20]([OH:30])[CH:19]=1)=[O:12])=O)(C)(C)C.FC(F)(F)C(O)=O>ClC(Cl)C>[NH2:8][CH2:9][CH2:10][C:11]([N:13]([CH2:14][C:15]([NH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([O:26][CH2:27][C:28]#[N:29])=[O:25])=[C:20]([OH:30])[CH:19]=1)=[O:31])[CH2:32][C:33](=[O:34])[NH:35][CH2:36][C:37]1[CH:48]=[CH:47][C:40]([C:41]([O:43][CH2:44][C:45]#[N:46])=[O:42])=[C:39]([OH:49])[CH:38]=1)=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 9810099HCID 9810099, compound

Product 1

HCID 9851229HCID 9851229, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

The crude Cyanomethyl 4-{[2-(3-[(tert-Butoxy)carbonylamino]-N-{[N-({4-[(cyanomethyl)oxycarbonyl]-3-hydroxyphenyl}methyl)carbamoyl]methyl}propanoyl-amino)acetylamino]methyl}-2-hydroxybenzoate from above was dissolved in 20 mL of dichloroethane and 10 mL of trifluoroacetic acid (26.0 mmole) was added. The deprotection reaction was stirred for 2 hours at room temperature. Dichloroethane and trifluoroacetic acid were removed in vacuo. The resulting oil was dissolved in 10 mL of ethyl acetate, and the resulting solution was added dropwise to 150 mL of rapidly stirred methyl tert-butyl ether. The product precipitated over the course of one hour and was collected by filtration, washed with methyl tert-butyl ether and dried in vacuo under a high vacuum. Obtained 2.78 grams (65% for two steps) of product as a white solid.

Workup

  1. customThe deprotection reaction
  2. customDichloroethane and trifluoroacetic acid were removed in vacuo
  3. dissolutionThe resulting oil was dissolved in 10 mL of ethyl acetate
  4. additionthe resulting solution was added dropwise to 150 mL of rapidly stirred methyl tert-butyl ether
  5. customThe product precipitated over the course of one hour
  6. filtrationwas collected by filtration
  7. washwashed with methyl tert-butyl ether
  8. customdried in vacuo under a high vacuum
  9. customObtained 2.78 grams (65% for two steps) of product as a white solid

Sources & evidence

ORD record
ord-bca5cc3b98db4042905f525567415289
Source dataset
uspto-grants-2002_07
Patent number
US06414122B1

Reaction notes

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